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SML1958

Sigma-Aldrich

BAY 60-6583

≥98% (HPLC)

Synonym(s):

2-[[6-Amino-3,5-dicyano-4-[4-(cyclopropylmethoxy)phenyl]-2-pyridinyl]thio]-acetamide, BAY 606583, BAY 60–6,583, BAY606583, BR 4887, BR4887

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About This Item

Empirical Formula (Hill Notation):
C19H17N5O2S
CAS Number:
910487-58-0
Molecular Weight:
379.44
MDL number:
MFCD22683833
UNSPSC Code:
12352200

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

NC1=C(C#N)C(C2=CC=C(OCC3CC3)C=C2)=C(C#N)C(SCC(N)=O)=N1

InChI

1S/C19H17N5O2S/c20-7-14-17(12-3-5-13(6-4-12)26-9-11-1-2-11)15(8-21)19(24-18(14)23)27-10-16(22)25/h3-6,11H,1-2,9-10H2,(H2,22,25)(H2,23,24)

InChI key

ZTYHZMAZUWOXNC-UHFFFAOYSA-N

Biochem/physiol Actions

BAY 60-6583 is a potent adenosine receptor A2b (A2bR) partial agonist (Ki against 0.3 nM [3H]PSB-603 for binding human/mouse/rat A2bR = 114/136/100 nM) that selectively induces cAMP-dependent transcription activity in CHO transfectants expressing human A2bR (EC50 ~100 nM), but not A1R or A2aR, while exhibiting no affinity toward human/rat/mouse A2aR. BAY 60-6583 also displays low-affinity antagonistic activity toward A1R (Ki against 1 nM [3H]CCPA for binding human/mouse/rat A1R = 387/351/514 nM; IC50 = 7.4 μM against 100 nM CCPA-induced hA1R β-arrestin recruitment) and A3R (Ki against 10 nM [3H]NECA for binding human/mouse/rat A3R = 223/3920/2750 nM; IC50 = 6.7 μM against 30 nM Cl-IB-MECA-induced hA3R β-arrestin recruitment). BAY 60-6583 is widely administered in animals in vivo via i.p. (0.1-80 mg/kg) or i.v. (0.2-2 mg/kg) for studying A2bR-mediated biological responses.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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